8-ISOPROSTAGLANDIN E2

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H32O5
Molecular Weight	352.4651
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@H]1C\C=C/CCCC(O)=O

InChI

InChIKey=XEYBRNLFEZDVAW-CLQOMRTCSA-N

InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17+,19+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22959706
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15650411 | https://www.ncbi.nlm.nih.gov/pubmed/26209241 | https://www.ncbi.nlm.nih.gov/pubmed/9717718 |

8-Iso-prostaglandin E2 (8-iso-PGE2) is one of the several isoprostanes produced from arachidonic acid during lipid peroxidation. Isoprostanes are a group of stable prostaglandin-like compounds produced by free radical-catalyzed, non-enzymatic peroxidation of arachidonic acid, which are used as markers of oxidative stress in several human diseases, including diabetes. In addition, 8-iso-prostaglandin E2 is biologically active compound involved in contraction of vascular smooth muscle and activation of platelets. 8-iso-PGE2 has been demonstrated to be the most potent vasoconstrictor isoprostane on the human umbilical artery and vein, activating the TPα isoform, which is present in the human umbilical vein and platelets. 8-iso-prostaglandin E2 stimulates human umbilical vein endothelial cells to specifically bind monocytes and this effect is mediated by cyclic AMP/protein kinase A- and p38 MAP kinase-dependent pathways and is independent of the classical inflammatory NFkappaB pathway.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Thromboxane A2 receptor 19 Target ID: CHEMBL2069 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22959706	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Aspirin exacerbated respiratory disease 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26209241	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Isoprostanes as physiological mediators of transition to newborn life: novel mechanisms regulating patency of the term and preterm ductus arteriosus.	2012 Aug	22565502

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Human umbilical cords were collected from healthy and normotensive women after full-term vaginal or caesarean deliveries. Cumulative concentration-response curves to 8-iso-PGE2 were obtained by addition to the organ bath in 0.25 log10 increments (1, 1.7, 3, 5.5, and 10 nmol/l etc. to 30 μmol/l). Concentrationresponse curves to 8-iso-PGE2 were obtained alone and in the presence of EV-077 (1, 3, 10 and 30 nmol/l) added to the solution 30 min before the agonist. At the end of each concentration-response curve, serotonin (5-HT, 10 μmol/l) was applied to determine the tissue maximal contractile response. The isoprostane 8-iso-PGE2 evoked concentration-dependent contraction of the human umbilical artery, yielding a pEC50 value of 7.33±0.05

Name

Type

Language

8-ISOPROSTAGLANDIN E2

Common Name

English

PROSTA-5,13-DIEN-1-OIC ACID, 11,15-DIHYDROXY-9-OXO-, (5Z,8.BETA.,11.ALPHA.,13E,15S)-

Systematic Name

English

DINOPROSTONE IMPURITY, 8-ISODINOPROSTONE- [USP IMPURITY]

Common Name

English

(Z)-7-((1S,2R,3R)-3-HYDROXY-2-((E)-(3S)-3-HYDROXYOCT-1-ENYL)-5-OXOCYCLOPENTYL)HEPT-5-ENOIC ACID

Systematic Name

English

DINOPROSTONE IMPURITY B [EP IMPURITY]

Common Name

English

8-ISO-PGE2

Common Name

English

15-E2T-ISOPROSTANE

Common Name

English

8-ISODINOPROSTONE

Common Name

English

Code System Code Type Description

FDA UNII

W1ANC8Q5NW